Hydrochloric Acid → 5-(5-Hydroxy-pent-1-ynyl)-indole-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To 3.73 g (12.5 mmol) 5-Bromo-indole-1-carboxylic acid tert-butyl ester in 25 ml piperidine were added 722 mg (0.63 mmol) tetrakis-(triphenylphosphine)-palladium and 120 mg (0.625 mmol) CuI. The solution was purged with argon, and was heated to 80° C. over a period of 45 min, during which 0.9 ml (9.4 mmol) 4-pentynol were added. Additional 0.9 ml (9.4 mmol) 4-pentynol were added and the mixture was stirred at 80° C. for 2 h, poured on ice water and 2M HCl was added. The inorganic phase was extracted with ether, the organic phases were washed with water and dried over Na2SO4. Purification on silica gel yielded 2.9 g (77%) 5-(5-Hydroxy-pent-1-ynyl)-indole-1-carboxylic acid tert-butyl ester as brown oil, MS: 299 (M).

Provenance & Evidence